EP0413064A1 - Préparation de 2-phényl-propan-1,3-diol et son dicarbamate - Google Patents

Préparation de 2-phényl-propan-1,3-diol et son dicarbamate Download PDF

Info

Publication number: EP0413064A1
Authority: EP; European Patent Office
Prior art keywords: phenyl; propanediol; nitromethylbenzene; nitro; benzaldehyde
Prior art date: 1987-06-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP89308266A

Other languages

German (de)

English (en)

Other versions

EP0413064B1 (fr

Inventor

Frank J. Stiefel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Viatris Inc

Original Assignee

Carter Wallace Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-06-03

Filing date

1989-08-15

Publication date

1991-02-20

1989-08-15 Application filed by Carter Wallace Inc filed Critical Carter Wallace Inc

1989-08-15 Priority to DE1989607596 priority Critical patent/DE68907596T2/de

1989-08-15 Priority to AT89308266T priority patent/ATE91486T1/de

1991-02-20 Publication of EP0413064A1 publication Critical patent/EP0413064A1/fr

1993-07-14 Application granted granted Critical

1993-07-14 Publication of EP0413064B1 publication Critical patent/EP0413064B1/fr

2009-08-15 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

BPBDZXFJDMJLIB-UHFFFAOYSA-N 2-phenylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1 BPBDZXFJDMJLIB-UHFFFAOYSA-N 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 27
VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims abstract description 21
VTWKXBJHBHYJBI-VURMDHGXSA-N (nz)-n-benzylidenehydroxylamine Chemical compound O\N=C/C1=CC=CC=C1 VTWKXBJHBHYJBI-VURMDHGXSA-N 0.000 claims abstract description 18
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 18
AJRYCRIQZBMNEO-UHFFFAOYSA-N 2-nitro-2-phenylpropane-1,3-diol Chemical compound OCC(CO)([N+]([O-])=O)C1=CC=CC=C1 AJRYCRIQZBMNEO-UHFFFAOYSA-N 0.000 claims abstract description 17
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 9
NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
230000001590 oxidative effect Effects 0.000 claims abstract description 5
WKGXYQFOCVYPAC-UHFFFAOYSA-N felbamate Chemical compound NC(=O)OCC(COC(N)=O)C1=CC=CC=C1 WKGXYQFOCVYPAC-UHFFFAOYSA-N 0.000 claims abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
239000000203 mixture Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
150000002923 oximes Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
231100001261 hazardous Toxicity 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000011031 large-scale manufacturing process Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part

Definitions

This invention relates to the preparation of 2-phenyl-1, 3-propanediol and its dicarbamate.
the compound may be prepared by reacting 2-phenyl-1, 3-propanediol with phosgene to form the corresponding di-chlorocarbonate derivative with conversion to the dicarbamate by ammoniation.
Example 1 The preparation of benzaldehyde oxime by reacting hydroxylamine sulphate or hydroxylamine hydrochloride with benzaldehyde is illustrated in Example 1 hereinbelow. It has been optimized to provide a yield of over 95% and has been adapted to large scale production.
Example 2 The preparation of nitromethylbenzene by oxidation of benzaldehyde oxime is illustrated in Example 2 hereinbelow. Under controlled conditions, particularly temperatures of 80 o C to 90 o C, high yields and a high purity product are obtained.
the oxidation of benzaldehyde oxime is accomplished by using either 30% or 50% hydrogen peroxide or preferably commercial 35% peracetic acid in acetic acid as an oxidizing agent at controlled temperatures of from 80 o C to 90 o C to obtain high yields of high purity nitromethylbenzene.
the literature preparation of the nitrodiol involves the reaction of nitromethylbenzene with formaldehyde.
the reaction has been modified whereby sodium bicarbonate or sodium carbonate is used as the catalyst in lieu of the previously preferred sodium hydroxide. This change in catalyst has been found to allow a more controlled addition of the nitro compound to the formaldehyde with a lessening in the amount of polymeric materials formed in side reactions.
the removal of the aliphatic nitro group can be carried out by the hydrogenation of 2-nitro-2-phenyl-1, 3-propanediol in the presence of palladium on calcium carbonate at 345 kPa (50 psi).
the procedure permits the production 2-phenyl-1, 3-propanediol of high purity in yields of about 80%.
the method allows for large scale hydrogenation in standard reactors, capable of sustaining 862 kPa (125 psi). There is therefore a preferred pressure range of 345 kPa (50 psi) to 862 kPa (125 psi).
the final reaction of the present synthesis is the conversion of 2-phenyl-1, 3-propanediol to the desired dicarbamate. This step is illustrated in Example 5 hereinbelow.
phosgene to convert diols to dicarbamates is well known in the prior art.
an acid acceptor such as, for example dimethylaniline.
ethers for example, ethyl ether or tetrahydrofuran, replace the prior art acid acceptors thereby allowing the reaction to be run in solution with no precipitates to be separated and no necessity to recover and purify the acid acceptor.
the method of the present invention is quantitative and precludes contamination of the final product. Moreover, the synthesis is readily adaptable to commercial scale since the solution is easily pumped into ammonium hydroxide and removal of the organic solvents easily accomplished by distillation under reduced pressure.
the lower oxime layer is separated and the aqueous layer is extracted with 2 litres of toluene.
the oxime layer and toluene extract are washed twice with 1 litre of water.
the toluene is stripped and 1307 g. of the oxime at 98% purity for a 95% yield is obtained.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

EP89308266A 1987-06-03 1989-08-15 Préparation de 2-phényl-propan-1,3-diol et son dicarbamate Expired - Lifetime EP0413064B1 (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DE1989607596 DE68907596T2 (de)	1989-08-15	1989-08-15	Herstellung von 2-Phenyl-propan-1,3-diol und dessen Dicarbamat.
AT89308266T ATE91486T1 (de)	1989-08-15	1989-08-15	Herstellung von 2-phenyl-propan-1,3-diol und dessen dicarbamat.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/057,457 US4868327A (en)	1987-06-03	1987-06-03	Synthesis of 2-phenyl-1,3-propanediol

Publications (2)

Publication Number	Publication Date
EP0413064A1 true EP0413064A1 (fr)	1991-02-20
EP0413064B1 EP0413064B1 (fr)	1993-07-14

Family

ID=22010651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP89308266A Expired - Lifetime EP0413064B1 (fr)	1987-06-03	1989-08-15	Préparation de 2-phényl-propan-1,3-diol et son dicarbamate

Country Status (3)

Country	Link
US (1)	US4868327A (fr)
EP (1)	EP0413064B1 (fr)
ES (1)	ES2058540T3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993002030A1 (fr) *	1989-09-26	1993-02-04	Carter-Wallace, Inc.	Synthese de 1,3-propanediols a substitution 2-phenyle

Families Citing this family (15)

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Publication number	Priority date	Publication date	Assignee	Title
US5082861A (en) *	1989-09-26	1992-01-21	Carter-Wallace, Inc.	Method for the prevention and control of epileptic seizure associated with complex partial seizures
US5239121A (en) *	1992-09-16	1993-08-24	Ganes Chemicals Inc.	Process for the preparation of 2-aryl-1,3-propanediols
US5250744A (en) *	1992-09-16	1993-10-05	Ganes Chemicals Inc.	Process for the preparation of 2-aryl-1,3-propanediols
US5395984A (en) *	1994-04-20	1995-03-07	Schering Corporation	Process for preparing 2-phenyl-1,3-propanediol
US5492930A (en) *	1994-04-25	1996-02-20	Schering Corporation	Method and formulation for treating CNS disorders
DK1156798T3 (da)	1999-02-09	2003-11-03	Univ Virginia	Felbamat-afledte forbindelser
WO2002056827A2 (fr) *	2000-10-25	2002-07-25	University Of Virginia Patent Foundation	Composes derives de felbamate substitue
US6538163B2 (en)	2001-05-11	2003-03-25	Rohm And Haas Company	Method for reduction of substituted malonates to diols
US20040082543A1 (en) *	2002-10-29	2004-04-29	Pharmacia Corporation	Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain
US20030166648A1 (en) *	2002-11-01	2003-09-04	Macdonald Timothy L	Felbamate derived compounds
EP1888570A4 (fr) *	2005-04-21	2010-05-19	Medpointe Healthcare Inc	Procedes de synthese de composes de dicarbamate et de produits intermediaires dans la formation de ces derniers
US7884227B2 (en) *	2007-10-26	2011-02-08	Navinta Llc	Felbamate with improved bulk density
WO2012032508A1 (fr)	2010-09-07	2012-03-15	Taro Pharmaceutical Industries Ltd.	Procédé de préparation de 2-phényl-1,3-propanediol
IT202000011626A1 (it)	2020-05-19	2021-11-19	Consorzio Interuniversitario Naz Per La Reattivita’ Chimica E La Catalisi	Processo per la preparazione di poliuretani esenti da isocianati per co-polimerizzazione di dioli con urea in presenza di ossidi metallici come catalizzatori
CN112250580A (zh) *	2020-10-28	2021-01-22	上海昂卓新材料科技有限公司	一种2-硝基-2-取代苯基丙烷-1,3-二醇的制备方法

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US2884444A (en) *	1956-01-13	1959-04-28	Carter Prod Inc	2-phenyl-1,3 propane diol dicarbamate

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CA691753A (en) *		1964-08-04	Carter Products	Preparation of 2-phenyl-1,3 propanediol dicarbamate
CA630412A (en) *		1961-11-07	M. Berger Frank	2-phenyl-1,3, propanediol dicarbamate
GB800619A (en) *	1956-01-13	1958-08-27	Carter Prod Inc	Process for the preparation of 2-phenyl-1,3-propanediol dicarbamate
US3051744A (en) *	1959-10-07	1962-08-28	Syntex Corp	Carbamic acid esters
US3829463A (en) *	1971-05-19	1974-08-13	Upjohn Co	Oxime substituted carbanilates
IT1060246B (it) *	1976-04-23	1982-07-10	Alcar Srl	Processo per la preparazione di derivati para sostituiti dell acido alfa fenil propionico
US4272441A (en) *	1980-03-13	1981-06-09	Fmc Corporation	Preparation of carbamates

1987
- 1987-06-03 US US07/057,457 patent/US4868327A/en not_active Expired - Lifetime
1989
- 1989-08-15 ES ES89308266T patent/ES2058540T3/es not_active Expired - Lifetime
- 1989-08-15 EP EP89308266A patent/EP0413064B1/fr not_active Expired - Lifetime

Patent Citations (1)

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Publication number	Priority date	Publication date	Assignee	Title
US2884444A (en) *	1956-01-13	1959-04-28	Carter Prod Inc	2-phenyl-1,3 propane diol dicarbamate

Non-Patent Citations (6)

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Title
CHEMICAL ABSTRACTS, vol. 60, no. 9, 27th April 1964, abstract no. 10529c, Columbus, Ohio, US; E. ECKSTEIN et al.: "Fungicidal acitvity of some 2-nitropropane-1,3-diol derivatives", & BULL. ACAD. POLON. SCI., SER. SCI. CHIM. 11(12), 687-93(1963) *
CHEMICAL ABSTRACTS, vol. 82, no. 25, 23rd June 1975, page 485, abstract no. 170337a, Columbus, Ohio, US; & JP-A-74 28 500 (KYOWA YUKA CO., LTD) 26-07-1974 *
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HOUBEN-WEYL: "Methoden der organischen Chemie", vol. X/4, part 4, 1968, pages 55-77, Georg Thieme Verlag, Stuttgart, DE *
JOURNAL OF MEDICINAL CHEMISTRY, vol. 12, May, 1968, pages 462-472; B.J. LUDWIG et al.: "Carbamate derivatives related to meprobamate" *
TETRAHEDRON LETTERS, vol. 22, no. 18, 1981, pages 1705-1708, Pergamon Press Ltd, GB; N. ONO et al.: "A new synthetic method: direct replacement of the nitro group by hydrogen or deuterium" *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993002030A1 (fr) *	1989-09-26	1993-02-04	Carter-Wallace, Inc.	Synthese de 1,3-propanediols a substitution 2-phenyle

Also Published As

Publication number	Publication date
US4868327A (en)	1989-09-19
EP0413064B1 (fr)	1993-07-14
ES2058540T3 (es)	1994-11-01

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Publication	Publication Date	Title
EP0413064B1 (fr)	1993-07-14	Préparation de 2-phényl-propan-1,3-diol et son dicarbamate
US3361827A (en)	1968-01-02	Preparation of benzalacetophenone
WO1989012632A1 (fr)	1989-12-28	Procede de preparation de derives de sphingosine, et d'un aldehyde utilise dans lesdits derives
US3855306A (en)	1974-12-17	Process for the preparation of 2,4,5-trimethoxybenzaldehyde
EP0348223B1 (fr)	1995-06-07	Procédé pour la préparation de sérinol
US5072056A (en)	1991-12-10	Synthesis of 2-phenyl-1,3-propanediol
JP2580736B2 (ja)	1997-02-12	光学活性ヒドロキシベンジルアミン誘導体、その中間体およびその製造方法
US6417403B1 (en)	2002-07-09	Process for preparing chiral (s)-2,3-disubstituted-1-propylamine derivatives
EP0257151A1 (fr)	1988-03-02	Méthode pour la préparation de 2-phénylbenzotriazoles et de N-oxydes de 2-phénylbenzotriazoles
US4230869A (en)	1980-10-28	Process for preparing 5-(4-hydroxyphenyl)hydantoin
US5091595A (en)	1992-02-25	Reduction of diethyl phenylmalonate to 2-phenyl-1,3-propanediol
EP0858993B1 (fr)	2003-06-25	Procédé pour la fabrication d'acides cétoniques
CN115572272B (zh)	2024-05-07	非布司他及其醛基酯类中间体的制备方法
EP0349217A2 (fr)	1990-01-03	Procédé de préparation de bronopol
EP0739885B1 (fr)	2000-04-19	Procede de production d'acide 3-isoxazolecarboxylique
JP2857402B2 (ja)	1999-02-17	２―フェニル―１，３―プロパンジオール・ジカルバメートの調製方法
CA2278713A1 (fr)	1999-06-24	Procede de production de derives d'ester butyrique
US4154757A (en)	1979-05-15	Process for the manufacture of p-hydroxybenzyl cyanide
JPH0223535B2 (fr)	1990-05-24
AU9124991A (en)	1993-02-23	Synthesis of 2-phenyl substituted-1,3-propanediols
IE912619A1 (en)	1993-01-27	Synthesis of 2-phenyl substituted-1, 3-propanediols
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US6509493B1 (en)	2003-01-21	Method for producing atropic acid ethyl ester
US5250744A (en)	1993-10-05	Process for the preparation of 2-aryl-1,3-propanediols
JPS60190729A (ja)	1985-09-28	トリメチロ−ルヘプタンの製法

EP0413064A1 - Préparation de 2-phényl-propan-1,3-diol et son dicarbamate - Google Patents

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